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1.25 Lignans: Biosynthesis and Function 1.25 Lignans: Biosynthesis and Function NORMAN G. LEWIS and LAURENCE B. DAVIN Washington State University, Pullman, WA, USA 0[14[0 INTRODUCTION 539 0[14[1 DEFINITION AND NOMENCLATURE 539 0[14[2 EVOLUTION OF THE LIGNAN PATHWAY 531 0[14[3 OCCURRENCE 534 0[14[3[0 Li`nans in {{Early|| Land Plants 534 0[14[3[1 Li`nans in Gymnosperms and An`iosperms "General Features# 536 0[14[4 OPTICAL ACTIVITY OF LIGNAN SKELETAL TYPES AND LIMITATIONS TO THE FREE RADICAL RANDOM COUPLING HYPOTHESIS 536 0[14[5 707? STEREOSELECTIVE COUPLING] DIRIGENT PROTEINS AND E!CONIFERYL ALCOHOL RADICALS 541 0[14[5[0 Diri`ent Proteins Stipulate Stereoselective Outcome of E!Coniferyl Alcohol Radical Couplin` in Pinoresinol Formation 541 0[14[5[1 Clonin` of the Gene Encodin` the Diri`ent Protein and Recombinant Protein Expression in Heterolo`ous Systems 543 0[14[5[2 Sequence Homolo`y Comparisons 543 0[14[5[3 Comparable Systems 543 0[14[5[4 Perceived Biochemical Mechanism of Action 546 0[14[6 PINORESINOL METABOLISM AND ASSOCIATED METABOLIC PROCESSES 547 0[14[6[0 Sesamum indicum] "¦#!Piperitol\ "¦#!Sesamin\ and "¦#!Sesamolinol Synthases 547 0[14[6[1 Magnolia kobus] Pinoresinol and Pinoresinol Monomethyl Ether O!Methyltransferase"s# 550 0[14[6[2 Forsythia intermedia and Forsythia suspensa 551 0[14[6[2[0 "¦#!Pinoresinol:"¦#!lariciresinol reductase 552 0[14[6[2[1 "−#!Secoisolariciresinol dehydro`enase 554 0[14[6[2[2 Matairesinol O!methyltransferase 556 0[14[6[3 Linum usitatissimum] "−#!Pinoresinol:"−#!Lariciresinol Reductase and "¦#!Secoisolariciresinol Glucosyltransferase"s# 557 0[14[6[4 Thuja plicata and Tsuga heterophylla] Pinoresinol:Lariciresinol Reductases and Other Enzymatic Conversions 557 0[14[6[5 Linum ~avum and Podophyllum hexandrum] Podophyllotoxin and its Pinoresinol Precursor 560 0[14[7 ARE DIRIGENT PROTEIN HOMOLOGUES INVOLVED IN OTHER 707? PHENOXY RADICAL COUPLING PROCESSES< 561 0[14[7[0 Li`ballinol "p!Coumarylresinol# and Related Structures 561 0[14[7[1 Syrin`aresinol and Medioresinol 562 0[14[7[2 Pellia Liverwort Li`nans 562 0[14[7[3 Li`nanamides 562 0[14[7[4 Guaiaretic Acid\ Ste`anacin\ and Gomisin A 565 0[14[8 MISCELLANEOUS COUPLING MODES] ARE DIRIGENT PROTEINS ALSO INVOLVED< 566 528 539 Li`nans] Biosynthesis and Function 0[14[09 704? AND 70O03? COUPLING OF MONOLIGNOLS AND ALLYLPHENOLS AND THEIR ASSOCIATED METABOLIC PROCESSES 567 0[14[09[0 Formation and Metabolism of 704? and 70O03? Linked Li`nans 579 0[14[09[0[0 Phenylcoumaran 60O03? rin` reduction 570 0[14[09[0[1 Allylic 607? bond reduction 571 0[14[09[1 Re`iospeci_c O!Demethylation at Carbon 2? and Monosaccharide Functionalization 572 0[14[09[2 Acylation 573 0[14[00 MIXED DIMERS CONTAINING MONOLIGNOLS AND RELATED MONOMERS 574 0[14[01 LIGNANS AND SESQUILIGNANS] WHAT IS THE RELATIONSHIP TO LIGNIN FORMATION< 576 0[14[02 PHYSIOLOGICAL ROLES IN PLANTA 589 0[14[02[0 Antioxidant Properties 589 0[14[02[1 Antifun`al and Antimicrobial Effects 580 0[14[02[2 Insecticides\ Nematocides\ Antifeedants\ and Poisons 582 0[14[02[3 Allelopathy 584 0[14[02[4 Cytokinin!like Activities 584 0[14[02[5 Constitutive and Inducible "Oli`omeric# Li`nan Deposition and Nonstructural Infusions\ {{Abnormal|| and {{Stress|| Li`nins 585 0[14[03 ROLES IN HUMAN NUTRITION:HEALTH PROTECTION AND DISEASE TREATMENT 587 0[14[03[0 Nutrition:Health and Protection a`ainst Onset of Breast and Prostate Cancers] Secoisolariciresinol\ Matairesinol\ and Sesamin 587 0[14[03[1 Antitumor Properties] Podophyllotoxin and other 707? Li`nans 690 0[14[03[2 Hepatotoxic Preventive Effects 691 0[14[03[3 Antiviral Properties 691 0[14[03[4 Miscellaneous Health Bene_ts] Anti!in~ammatory\ Antiasthmatic\ and Antidepressant Effects 693 0[14[04 CONCLUDING REMARKS 695 0[14[05 REFERENCES 696 0[14[0 INTRODUCTION The lignans are a very common\ structurally diverse\ group of plant natural products of phenyl! propanoid origin[0 They display important physiological functions in planta\ particularly in plant defense\1Ð4 and are most e.cacious in human nutrition and medicine\ given their extensive health protective and curative properties[5Ð8 This chapter primarily describes the intricate biochemical pathways established in lignan biosyn! thesis\ particularly as regards phenylpropanoid coupling[ It must be emphasized at the outset\ however\ that the biochemical outcome of enzymatic coupling was previously widely held to result only in formation of randomly linked racemic products[ This hypothesis\ originally adopted for lignin biopolymer formation "but see Chapter 2[07#\ could not explain the observed optical activities of the vast majority of naturally occurring lignans "discussed in Section 0[14[4#[ In contrast\ research has established that most\ if not all\ phenylpropanoid coupling reactions catalyzed by puri_ed plant proteins and enzymes in vitro can be either regio! or stereoselectively controlled\ as are their subsequent stereospeci_c metabolic conversions[ This contribution therefore attempts to summarize the progress made in this area\ as well as in providing an assessment of the rapidly growing importance of lignans in plant growth\ development\ and survival\ and in human usage[ 0[14[1 DEFINITION AND NOMENCLATURE Around the turn of the nineteenth century\ a number of plant phenolic substances from various species were isolated and given trivial names\ prior to their chemical structures being determined[ One of these\ guaiaretic acid\ from guaiacum resin obtained from Guaiacum of_cinale heartwood\ was later shown to contain the skeletal formula "0# by Schroeter et al[09 It was subsequently proposed00 that it and related compounds represented a unique class of dimeric phenylpropanoid substances linked exclusively through 707? bonds\ e[g[\ "1#[ In order to provide a system for their classi_cation\ Haworth00 introduced the term {{lignane|| "later shortened to lignan# to de_ne these substances^ they were considered to result from regiospeci_cally linking two {{cinnamyl|| "C5C2# molecules to give compounds such as guaiaretic acid "0# and pinoresinols "2a\b#[ This initial classi! _cation\ unfortunately\ failed to account for either other dimeric lignan skeletal types that were Li`nans] Biosynthesis and Function 530 present in many plant species and tissues or much larger molecules "oligomeric lignans# that could also exist[ A derivative term\ neolignan\ was introduced to account for the other coupling modes\ e[g[\ megaphone "3#"700? linked#\ dehydrodiconiferyl alcohols "4a\b#"704? linked# and erythro:threo guaiacylglycerol 70O03? coniferyl alcohol ethers "5a\b#"70O03? linked#\01Ð03 but this was later modi_ed to encompass only presumed allylphenol!derived coupling products\ such as the lignans OMe OMe 6 7 9 OH HO MeO 5 1 8 8 4 8' O O 2 8' HO 7' 3 9' 1' 8' 8 6' 2' 8 8' 3' O O 5' 4' OMe OH HO OH OMe OMe (1) Guaiaretic acid (2) (3a) (+)-Pinoresinol (3b) (–)-Pinoresinol [α]D = –94˚ α 22 α 25 [ ] D = +61.6˚ (CHCl3) [ ]D = –34.7˚ (CHCl3, c = 0.91) (Guaiacum officinale) (Forsythia europaea) (Daphne tangutica) OH OH 4' O OH 8 O HO OH 5' MeO OH 1' MeO 8 8 OMe O OMe OMe MeO HO OH OMe OMe (4) (–)-Megaphone (5a,b) (±)-Dehydrodiconiferyl alcohols (6a,b) (±)-erythro/threo Guaiacylglycerol α 27 8–O–4' coniferyl alcohol ethers [ ]D = –23.0˚ (EtOH, c = 0.15) (Aniba megaphylla) O O OH OH OH O O 8 55' 3O 4' MeO O 7' OH 71' OMe MeO O 8 O 2' O MeO OMe (7) Magnolol (8) Isomagnolol (9) Chrysophyllon 1A (10) (Magnolia virginiana) (Sassafras randaiense) (Licaria chrysophylla) (Virola sebifera) MeO HO OH 8' O OMe 7' 7 2 O MeO 3' O 8 OMe OH MeO MeO MeO O 9 MeO OMe OMe O (11) Isoasatone (12) Lancilin (13) (–)-Cryptoresinol α 20 (Aniba lancifolia) α 25 [ ]D = 0˚ [ ]D = –170.4˚ (MeOH, c = 1.25) (Asarum taitonense) (Cryptomeria japonica) 531 Li`nans] Biosynthesis and Function OMe H MeO 8' HO OH 8 O 8 8' 8' RO 7' MeO 7 OH OH O OMe OMe O 8 OH 9 MeO OMe OMe OH (16) (–)-Nortrachelogenin, R = H (14) (–)-Hydroxysugiresinol (15) Pachypostaudin A [α]17 = –16.8˚ (EtOH, c = 0.178) [α]25 = –19˚ (EtOH, c 1) [α]24 = 0˚ (CHCl , c = 0.8) D D D 3 (17) (–)-Trachelogenin, R = Me (Sequoia sempervirens) (Pachypodanthium staudtii) α 23 [ ] D = –43.3˚ (EtOH, c = 0.25) (Trachelospermum asiaticum) "3# and "6#Ð"01#[04 As a further complication\ the term norlignan05 was adopted to depict lignan!like metabolites which lacked either a carbon at the C!8 and:or C!8? positions\ e[g[\ cryptoresinol "02#\06 hydroxysugiresinol "03#\07 and pachypostaudin A "04#\08 or a methyl group on the aromatic methoxyl\ e[g[\ nortrachelogenin "05#19\10 versus trachelogenin "06#[19\11 It is now well established that the products of phenylpropanoid coupling have a range of structural motifs7\03\04\12\13 and molecular sizes\14Ð29 rather than being restricted to 707? linked moieties as previously contemplated[ Moreover\ since there appear to be only a relatively small number of distinct skeletal forms\ the term lignan can be conveniently used to encompass all skeletal types\ provided that the precise linkage type is stipulated\ e[g[\ 707?\ 700?\ 704?\ 70O03?\ 404?\ 20O03?\ 600?\ 706?\ 004?\ and 10O02?[ Of the various lignan types known\ however\ those that are 707? linked appear to be the most widespread in nature\ based on current chemotaxonomic data^12 they can also be further subdivided into the substituted furofurans\ tetrahydrofurans\ dibenzylbutanes\ dibenzylbutyrolactones\ aryltetrahydronaphthalenes\ arylnaphthalenes\ dibenzocyclooctadienes\ etc[ "e[g[\ Structures "07#Ð "14##[ Although not lignans proper\ there are also related natural products of mixed metabolic origin\ e[g[\ so!called ~avonolignans20Ð22 which are described in Section 0[14[00[
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